One of the most successful entrepreneurs in the world of car and home insurance he may be, but 65-year-old Esure founder Peter Wood will forever be cursed by television viewers for dreaming up some of the most irritating – yet memorable – adverts of the last three decades.

It is thanks to him we have endured Michael Winner's "Calm down dear" ads, the beehive-haired singing trio in a Sheila's Wheels pink Cadillac, and the car-horn jingle from Direct Line's red telephone-on-wheels.

As if these were not offence enough, Esure's joint venture price comparison business Go Compare has given viewers the fictional Italian tenor Gio Compario. Revelling in the irritation Compario inspired, the company went on to broadcast commercials featuring celebrities attempting to assassinate him with a bazooka.

Multi-millionaire Wood, has always refused to hire a marketing director – both at Esure and at his earlier business Direct Line – and has personally taken charge of publicity campaigns for almost all his career.

In the late 1980s, working with advertising experts Sian Vickers and Chris Wilkins, Wood hammered home the arrival of Britain's first telephone-only insurer, with the creation of Direct Line's speeding red phone on wheels.

Three years later he started Esure and the adverts, this time fronted by the late Michael Winner, gave the restaurant critic and film director his "calm down dear, it's only a commercial" catch phrase. Winner had become the face of the brand after ringing his friend Wood to complain about the standard of previous adverts, and insisting he could do much better.

It was not the first time the Death Wish director had rung Wood to gripe. The two men had become friends after the notorious curmudgeon had demanded call centre staff put him through to the boss of Direct Line.It was not until Wood threatened to cancel Winner's policy that the restaurant critic withdrew the complaint and suggested they settle the matter over a lunch – leading to a long friendship.

Winner was dropped for a spell by Esure in favour of an animated mouse on wheels. However, that campaign was successfully challenged in the courts by RBS, which argued it breached trademark protections and was too similar to the Direct Line wheeled phone. Winner was re-hired.

According to Esure, Winner, who passed away last month, at one stage wrote to Wood expressing his wish that his "Calm down dear" adverts carry on being aired after his death. Wood is still considering whether to air what an Esure spokesman called "RIP Michael Winner" advert.